JP7334029B2 - Self-emulsifying polyisocyanate composition and coating composition using the same - Google Patents

Description

The present invention relates to a self-emulsifying polyisocyanate composition, a coating composition obtained therefrom and a coating film thereof.

Conventionally, polyisocyanate is known as a curable composition used as adhesives, paints, etc., but hydrophobic polyisocyanate having an isocyanurate structure is modified with a nonionic hydrophilic group-containing monofunctional alcohol compound, and is dissolved in water. Emulsified and dispersed for use. (See Patent Document 1, for example). In the case of such a composition, there is a problem that a strong shearing force such as high-speed stirring is required in order to uniformly incorporate the polyisocyanate into the aqueous medium. In addition, when a strong shearing force is not applied by high-speed stirring or the like, when dispersing polyisocyanate in an aqueous medium, there is also a problem that the proportion of polyisocyanate dispersed in water (hereinafter referred to as "water dispersity") is low. . Therefore, a self-emulsifying polyisocyanate that is easy to disperse in water has been disclosed by modifying the polyisocyanate with an anionic hydrophilic group-containing amine instead of a nonionic hydrophilic group-containing monofunctional alcohol (for example, Patent Document 2. reference). However, the obtained self-emulsifying polyisocyanate has a high viscosity, and when a strong shearing force such as high-speed stirring is not applied, the polyisocyanate does not have a sufficient degree of water dispersion. In addition, the obtained paint also had a problem that the dispersion stability was insufficient and the water-dispersed self-emulsifying polyisocyanate component sedimented.

JP-A-61-291613 Japanese Patent Publication No. 2003-533566

The present invention has been made based on the above circumstances, and its object is to improve the water dispersion degree and water dispersion stability of the paint without requiring a strong shearing force due to high-speed stirring or the like when dispersed in an aqueous medium. To provide a self-emulsifying polyisocyanate composition excellent in

As a result of intensive studies by the present inventors, it was found that the above problems were solved by a self-emulsifying polyisocyanate composition obtained from a specific anionic compound (a), an organic polyisocyanate (b), and an amine compound (c). The inventors have found the present invention.

That is, the present invention includes embodiments shown in [1] to [5] below.

[1] A self-emulsifying polyisocyanate composition obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c), wherein the anionic compound (a) is represented by the following formula 1 , a self-emulsifying polyisocyanate composition, characterized in that the content of sulfo groups in the composition is 0.10 to 0.35 mmol/g.

(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbon atoms contained is 3 or more and 6 or less.)

[2] The self-emulsifying polyisocyanate composition according to [1] above, wherein the mass fraction of isocyanate groups in the organic polyisocyanate (b) is 10 to 35 mass%.

[3] The self-emulsifying polyisocyanate composition according to [1] or [2] above, wherein the organic polyisocyanate (b) contains an isocyanurate-modified polyisocyanate of hexamethylene diisocyanate.

[4] A coating composition obtained from the self-emulsifying polyisocyanate composition according to any one of [1] to [3] above and a main agent.

[5] A coating film obtained from the coating composition described in [4] above.

According to the present invention, it is possible to obtain a self-emulsifying polyisocyanate composition excellent in water dispersion degree and water dispersion stability.

The present invention will be described in detail below.

The self-emulsifying polyisocyanate composition of the present invention is obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c).

<Anionic compound (a)>
In the present invention, the anionic compound (a) is represented by the following formula 1 and is a hydrophilizing agent for producing a self-emulsifying polyisocyanate composition capable of imparting hydrophilicity to the organic polyisocyanate (b).

(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbon atoms contained is 3 or more and 6 or less.)
Examples of straight-chain alkyl groups represented by R ¹ and having a total carbon number of 3 or more and 6 or less include propyl, butyl, pentyl, and hexyl groups.

One or more carbon atoms in the straight-chain alkyl group represented by R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and the total number of carbon atoms is 3 or more and 6 or less Examples of groups include 2-methoxyethyl group, 2-ethoxyethyl group, 2-propoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-propoxypropyl group, 4-methoxybutyl group, 4-ethoxy Examples include butyl group, 2-(2-methoxyethoxy)ethyl group, 2-(2-ethoxyethoxy)ethyl group and the like.

Examples of the anionic compound (a) include 3-(propylamino)propanesulfonic acid, 3-(butylamino)propanesulfonic acid, 3-[(3-methoxypropyl)amino]propanesulfonic acid, 3-[(3 -ethoxypropyl)amino]propanesulfonic acid, 3-(hexylamino)propanesulfonic acid and the like, and it is preferable to use at least one selected from these groups. The content of sulfo groups in the self-emulsifying polyisocyanate composition is 0.10 to 0.35 mmol/g. Within this range, it is possible to obtain a paint having improved water dispersion and excellent water dispersion stability.

In the anionic compound (a) used in the present invention represented by Formula 1, the active hydrogen of the sulfo group in the molecule is neutralized with the amine in the molecule to form an internal salt represented by Formula 1a. , the anionic compound (a) of the present invention contains an internal salt represented by Formula 1a. The anionic compound (a) of the present invention is represented herein as Formula 1.

(In the formula, R ¹ has the same meaning as above.)
The anionic compound (a) can be prepared with reference to methods described in literature (eg, US Patent Application Publication No. 20070010573).

<Organic polyisocyanate (b)>
Examples of the organic polyisocyanate (b) used in the present invention include organic polyisocyanates selected from aromatic polyisocyanates, araliphatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates. These isocyanurate-modified polyisocyanates, allophanate-modified polyisocyanates, uretdione-modified polyisocyanates, urethane-modified polyisocyanates, biuret-modified polyisocyanates, urethymine-modified polyisocyanates, acyl urea-modified polyisocyanates, etc. may be used alone or in combination of two or more. can do. Further, when considering weather resistance, aliphatic polyisocyanates, alicyclic polyisocyanates, and modified polyisocyanates thereof are preferable, and from the viewpoint of durability of the coating film and adhesion to the substrate, aliphatic polyisocyanates, or It is preferable to use at least one selected from the group consisting of isocyanurate-modified polyisocyanates and allophanate-modified polyisocyanates of alicyclic polyisocyanates. Considering glossiness, it is preferable to use at least one selected from the group consisting of isocyanurate-modified polyisocyanate of hexamethylene diisocyanate and allophanate-modified polyisocyanate.

<Aromatic polyisocyanate>
Examples of aromatic polyisocyanates include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate/2,6-tolylene diisocyanate mixture, 4,4'-diphenylmethane diisocyanate, 2 ,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate/4,4'-diphenylmethane diisocyanate mixture, m-xylylene diisocyanate, p-xylylene diisocyanate, 4,4'-diphenyl ether diisocyanate, 2-nitrodiphenyl-4 ,4′-diisocyanate, 2,2′-diphenylpropane-4,4′-diisocyanate, 3,3′-dimethyldiphenylmethane-4,4′-diisocyanate, 4,4′-diphenylpropane diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, naphthylene-1,4-diisocyanate, naphthylene-1,5-diisocyanate, 3,3'-dimethoxydiphenyl-4,4'-diisocyanate and the like.

<Aroliphatic polyisocyanate>
Examples of araliphatic polyisocyanates include 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, or mixtures thereof; 1,3-bis(1-isocyanato-1-methylethyl)benzene, 1,4 -bis(1-isocyanato-1-methylethyl)benzene, or mixtures thereof; ω,ω'-diisocyanato-1,4-diethylbenzene and the like.

<Aliphatic polyisocyanate>
Examples of aliphatic polyisocyanates include hexamethylene diisocyanate, tetramethylene diisocyanate, 2-methyl-pentane-1,5-diisocyanate, 3-methyl-pentane-1,5-diisocyanate, lysine diisocyanate, trioxyethylene diisocyanate and ethylene diisocyanate. , trimethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2′-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate , 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate-4-isocyanatomethyloctane, 2,5,7 -trimethyl-1,8-diisocyanate-5-isocyanatomethyloctane, bis(isocyanatoethyl) carbonate, bis(isocyanatoethyl) ether, 1,4-butylene glycol dipropyl ether-α,α'-diisocyanate, lysine diisocyanate methyl ester , 2-isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate and the like.

<Alicyclic polyisocyanate>
Examples of alicyclic polyisocyanates include isophorone diisocyanate, cyclohexyl diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2′-dimethyldicyclohexylmethane diisocyanate, bis(4-isocyanate -n-butylidene)pentaerythritol, hydrogenated hydrogenated dimer acid diisocyanate, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-5-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2- isocyanatomethyl-3-(3-isocyanatopropyl)-6-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-isocyanatomethyl-bicyclo[2 .2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-6-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-3-(3-isocyanatopropyl )-5-(2-isocyanatoethyl)-bicyclo-[2.2.1]-heptane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)-bicyclo-[2 .2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-(2-isocyanatoethyl)-bicyclo-[2.2.1]-heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl)-6-(2-isocyanatoethyl)-bicyclo-[2.2.1]-heptane, 2,5-bis(isocyanatomethyl)-bicyclo[2.2.1]-heptane, hydrogen hydrogenated diphenylmethane diisocyanate, norbornane diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate, hydrogenated hydrogenated tetramethylxylene diisocyanate, and the like.

Also, the mass fraction of isocyanate groups in the organic polyisocyanate (b) is preferably 10 to 35%, more preferably 15 to 24%.

<Amine compound (c)>
A tertiary amine is preferably used as the amine compound (c) of the present invention.

Tertiary amines include, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, dimethylcyclohexylamine, N-methylmorpholine, N-ethylmorpholine, N-methylpiperidine, N-ethylpiperidine, dimethylethanolamine, methyldiethanolamine, Mention may be made of tertiary monoamines such as triethanolamine, tertiary diamines such as 1,3-bis(dimethylamino)propane, 1,4-bis(dimethylamino)butane or N,N'-dimethylpiperazine. . In particular, tertiary monoamines are preferred, and tributylamine, dimethylcyclohexylamine, and N-methylmorpholine are more preferred, in terms of low reactivity to isocyanate.

Further, the amine compound (c) in the present invention is preferably used so that the molar equivalent ratio between the amino group contained in the amine compound (c) and the anionic compound (a) is 0.2 to 2.0. , 0.5 to 1.5.

<Production of self-emulsifying polyisocyanate composition>
In producing the self-emulsifying polyisocyanate composition, the order of mixing the anionic compound (a), the organic polyisocyanate (b), and the amine compound (c) is not particularly limited, and ordinary urethanization reaction conditions are applied. can do.

<Paint composition>
Next, the coating composition in the present invention will be explained.

The coating composition of the present invention is obtained from the self-emulsifying polyisocyanate composition of the present invention and a main ingredient.

As the main ingredient in the production of the coating composition of the present invention, a polymer compound which is liquid at room temperature and is insoluble in water or has no affinity for water can be preferably used. It is also possible to use water-soluble resins or water-based emulsions that are soluble in water or have a certain degree of affinity for water. These polymer compounds preferably contain hydroxyl groups, carboxyl groups or amino groups (hereinafter referred to as "nucleophilic groups") that react with isocyanate groups in the molecule, and in particular two or more nucleophilic groups per molecule. Those containing are preferred. Moreover, even if these polymer compounds do not contain nucleophilic groups capable of reacting with isocyanate groups, or even if they contain only a few nucleophilic groups, eventually the self-emulsifying polyisocyanate composition reacts with water. It becomes a polyurea compound, and a hard and tough coating film can be obtained. In addition, since the isocyanate group reacts with the nucleophilic groups present on the surface of the adherend, adhesion to the adherend is also improved. When a polymer compound containing a nucleophilic group capable of reacting with an isocyanate group at room temperature is used, the nucleophilic group in the polymer compound and the isocyanate group in the self-emulsifying polyisocyanate composition react to crosslink. Since it forms a structure, weather resistance, solvent resistance, etc. are further improved. The room temperature in the present invention is 5°C to 40°C.

Examples of such main agents include saturated or unsaturated polyester polyols, polycaprolactone polyols, saturated or unsaturated fatty acid-modified alkyd polyols, amino alkyd polyols, polycarbonate polyols, acrylic polyols, polyether polyols, epoxy polyols, fluorine-containing polyols, Further examples include saturated or unsaturated polyester resins, polycaprolactone resins, fatty acid-modified alkyd resins, aminoalkyd resins, polycarbonate resins, acrylic resins, polyether resins, epoxy resins, polyurethane resins, cellulose acetate butyrate resins, and fluorine-containing resins. be done.

In addition, water-soluble resins and water-based emulsions can also be suitably used as the main component. Epoxy resins, water-soluble cellulose derivatives, water-soluble polyesters, water-soluble lignin derivatives, water-soluble fluorine resins, water-soluble silicone resins, and the like.

The aqueous emulsion includes all so-called latexes and emulsions, such as styrene-butadiene copolymer latex, acrylonitrile-butadiene copolymer latex, methylmethacrylate-butadiene copolymer latex, chloroprene latex, polybutadiene latex, and the like. rubber latex, polyacrylate latex, polyvinylidene chloride latex, polybutadiene latex, or carboxyl-modified versions of these latexes, as well as polyvinyl chloride emulsion, urethane acrylic emulsion, silicone acrylic emulsion, vinyl acetate acrylic emulsion, polyurethane emulsions, acrylic emulsions, and the like.

Among these, acrylic polyols, acrylic resins, water-soluble acrylic resins, acrylic emulsions, urethane-acrylic emulsions, and polyurethane emulsions can be particularly preferably used in terms of coating film properties such as gloss and weather resistance and adhesive strength.

The number average molecular weight of the polymer compound as the main agent is preferably 1,000 to 1,000,000, more preferably 10,000 to 100,000.

<Blending ratio>
The blending ratio of the self-emulsifying polyisocyanate composition and the main agent in the production of the coating composition of the present invention is set to The molar ratio of isocyanate groups in the product to active hydrogen groups in the main agent is preferably 9:1 to 1:9, more preferably 6:4 to 4:6. Within this range, a coating film having better performance can be obtained.

Further, when using a main agent containing no active hydrogen groups in the molecule or containing only a few active hydrogen groups, the mass ratio of the self-emulsifying polyisocyanate composition and the main agent is preferably 1:9 to 5:5. 1:9 to 3:7 are more preferred. Within this range, a coating film having better performance can be obtained.

<Formulation method>
The main agent and the self-emulsifying polyisocyanate composition can be blended into the main agent as it is, once the self-emulsifying polyisocyanate composition is dispersed in water and then added, or dissolved in a solvent commonly used in the urethane field and then added. and the like. In the present invention, a method of dispersing the self-emulsifying polyisocyanate composition in water and then blending it with the main agent is preferred.

<Other additives>
The self-emulsifying polyisocyanate composition or coating composition in the present invention may optionally contain, for example, antioxidants, ultraviolet absorbers, pigments, dyes, flame retardants, hydrolysis inhibitors, lubricants, plasticizers, Additives such as agents, fillers, storage stabilizers, and film-forming aids can be appropriately added.

<Painting method>
The coating composition of the present invention can be applied by a conventional conventional coating method to obtain a coating film. For coating, an airless sprayer, an air sprayer, an electrostatic coating machine, immersion, a roll coater, a knife coater, a brush, or the like can be used.

The present invention will be described in more detail below with reference to synthesis examples, but the present invention should not be construed as being limited thereto.

[Production of anionic compound]
<Synthesis Example 1>
1,3-Propanesultone (6.02 g, 49.1 mmol) and propylamine (4.00 mL, 48.5 mmol) were weighed into a 200 mL flask equipped with a reflux tube and dissolved in tetrahydrofuran (44 mL). After the reaction solution was refluxed under an argon atmosphere for 11 hours, the volatile components were removed. The obtained solid was recrystallized from ethanol, and the precipitated white precipitate was collected by filtration, washed with tetrahydrofuran, and dried at 60° C. under reduced pressure to give 3-(propylamino)propanesulfonic acid (A-1). Obtained (4.55 g, 25.1 mmol, 51%). ¹ H NMR (400 MHz, DMSO-d6) δ (ppm): 8.48 (br, 2H), 3.05 (t, J=6.7 Hz, 2H), 2.84 (m, 2H), 2. 62 (m, 2H), 1.93 (tt, J = 6.5, 6.7Hz, 2H), 1.57 (tq, J = 7.7, 7.5Hz, 2H), 0.91 (t , J=7.5 Hz, 3H).

<Synthesis Example 2>
1,3-propanesultone (10.1 g, 82.7 mmol) and (3-methoxypropyl)amine (12.6 mL, 123 mmol) were weighed into a 200 mL flask equipped with a reflux tube and dissolved in tetrahydrofuran (60 mL). . After the reaction solution was refluxed for 2 hours under an argon atmosphere, the volatile components were removed. The resulting solid was dissolved in methanol, and the solution was passed through a strongly acidic ion-exchange resin (Amberlyst 15JWET, manufactured by Organo), followed by a weakly basic ion-exchange resin (Amberlyst A21, manufactured by Organo) until the solution became neutral. Organo) was added. The weakly basic ion exchange resin was filtered off and volatile components were removed to give 3-[(3-methoxypropyl)amino]propanesulfonic acid (A-2) (8.82 g, 41.7 mmol, 51%). ¹ H NMR (400 MHz, DMSO-d6) δ (ppm): 8.48 (br, 2H), 3.38 (t, J=6.0 Hz, 2H), 3.24 (s, 3H), 3. 04 (m, 2H), 2.93 (m, 2H), 2.61 (m, 2H), 1.92 (m, 2H), 1.79 (m, 2H).

<Synthesis Example 3>
1,3-Propanesultone (6.72 g, 55.0 mmol) and hexylamine (8.00 mL, 60.5 mmol) were weighed into a 200 mL flask equipped with a reflux tube and dissolved in tetrahydrofuran (60 mL). The reaction solution was refluxed for 2 hours under an argon atmosphere. After cooling to 25°C, the precipitated white precipitate was collected by filtration, washed with diethyl ether, and dried at 60°C under reduced pressure to obtain 3-(hexylamino)propanesulfonic acid (A-4) ( 6.73 g, 30.1 mmol, 55%). ¹ H NMR (400 MHz, DMSO-d6) δ (ppm): 8.47 (br, 2H), 3.03 (t, J=6.8 Hz, 2H), 2.86 (m, 2H), 2. 62 (m, 2H), 1.92 (m, 2H), 1.54 (m, 2H), 1.32-1.24 (m, 6H), 0.87 (t, J = 7.0Hz, 3H).

[Production of self-emulsifying polyisocyanate]
<Example 1>
An organic polyisocyanate (a polyisocyanate containing an isocyanurate form of hexamethylene diisocyanate, trade name: Coronate HXLV, isocyanate content: 23.5%) was added to a 0.1 L reactor equipped with a stirrer, thermometer, cooler, and nitrogen gas inlet tube. 2% by mass, manufactured by Tosoh Corporation), 0.68 g of A-1 obtained in Synthesis Example 1, and 0.48 g of dimethylcyclohexylamine were charged, stirred at 80 ° C. for 5 hours, and self-emulsifying polyisocyanate. P-1 was obtained. The sulfo group content of P-1 was 0.125 mmol/g, and the isocyanate content was 21.8% by mass.

Self-emulsifying polyisocyanates P-2 to P-12 were synthesized in the same manner as in Example 1. Tables 1 and 2 show the results.

・Coronate HXR (trade name): isocyanurate-containing polyisocyanate of hexamethylene diisocyanate, isocyanate content 21.8% by mass, manufactured by Tosoh Corporation ・CAPS: cyclohexylaminopropanesulfonic acid, manufactured by Tokyo Chemical Industry Co., Ltd. ・dimethylcyclohexylamine: reagent Special grade, manufactured by Tokyo Chemical Industry Co., Ltd.

<Viscosity evaluation>
The viscosities of the self-emulsifying polyisocyanate compositions (P-1 to 12) were measured using a B-type viscometer (TOKI SANGYO Co. LTD Viscometer TV-22). The results are shown in Tables 3-5.

<Particle size evaluation>
Weigh each self-emulsifying polyisocyanate composition (P-1 to 12) and purified water in a 30 ml sample bottle at a mass ratio of 1: 9 (so that the total amount is about 15 mL), and seal it for 20 seconds. and shaken up and down 60 times. The particle size of the resulting aqueous dispersion was evaluated with a particle size analyzer (Otsuka Electronics ELSZ-200). The results are shown in Tables 3-5. If the particle size is 250 nm or less, it can be said that the dispersion stability is good and the gloss of the coating film is good.

<Water dispersion evaluation>
Each self-emulsifying polyisocyanate composition (P-1 to 12) and purified water were precisely weighed in a tared 30 mL sample bottle at a mass ratio of 1: 9 (so that the total amount was about 15 mL). , and then shaken up and down by hand 60 reciprocations in 20 seconds. After that, the mixture was allowed to stand, the self-emulsifying polyisocyanate dispersed in water was removed together with the water, and the mass of the remaining self-emulsifying polyisocyanate composition that was not dispersed in water was measured. Using these measured values, the degree of water dispersion was obtained and evaluated by the following formula.

In the formula, (A) represents the mass (g) of the self-emulsifying polyisocyanate composition before shaking with water, and (B) represents the mass of the self-emulsifying polyisocyanate composition before shaking with water. It represents the value (g) obtained by subtracting the mass of the self-emulsifying polyisocyanate composition remaining without dispersing in water from (g).

The results are shown in Tables 3-5. If the degree of water dispersion is 80% or more, it can be said to be good.

Claims (6)

A self-emulsifying polyisocyanate composition obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c),
The anionic compound (a) is represented by the following formula 1,
the amine compound (c) is a tertiary monoamine,
The molar equivalent ratio between the amino group contained in the tertiary monoamine and the anionic compound (a) is 0.2 to 2.0,
A self-emulsifying polyisocyanate composition, characterized in that the content of sulfo groups in the composition is 0.10 to 0.35 mmol/g.
(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbons contained is 3.) A self-emulsifying polyisocyanate composition obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c),
The anionic compound (a) is represented by the following formula 1,
the amine compound (c) is a tertiary monoamine,
The molar equivalent ratio between the amino group contained in the tertiary monoamine and the anionic compound (a) is 0.2 to 2.0,
A self-emulsifying polyisocyanate composition, characterized in that the content of sulfo groups in the composition is 0.10 to 0.35 mmol/g.
(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbons contained is 4.) A self-emulsifying polyisocyanate composition obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c),
The anionic compound (a) is represented by the following formula 1,
the amine compound (c) is a tertiary monoamine,
The molar equivalent ratio between the amino group contained in the tertiary monoamine and the anionic compound (a) is 0.2 to 2.0,
A self-emulsifying polyisocyanate composition, characterized in that the content of sulfo groups in the composition is 0.10 to 0.35 mmol/g.
(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbon atoms contained is 5.) A self-emulsifying polyisocyanate composition obtained from an anionic compound (a), an organic polyisocyanate (b) and an amine compound (c),
The anionic compound (a) is represented by the following formula 1,
the amine compound (c) is a tertiary monoamine,
The molar equivalent ratio between the amino group contained in the tertiary monoamine and the anionic compound (a) is 0.2 to 2.0,
A self-emulsifying polyisocyanate composition, characterized in that the content of sulfo groups in the composition is 0.10 to 0.35 mmol/g.
(In the formula, R ¹ represents a straight-chain alkyl group. One or more carbon atoms in the group of R ¹ may be substituted with oxygen atoms so that the oxygen atoms are not adjacent, and R ¹ The total number of carbons contained is 6.) A coating composition obtained from the self-emulsifying polyisocyanate composition according to any one of claims 1 to 4 and a main agent. A coating film obtained from the coating composition according to claim 5 .